4-Bromo-1,1,1-trifluorobutane → 2-Methyl-2-(4,4,4-trifluoro-butylsulfanyl)-propionic acid ethyl ester

HRID 538638Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:12])[C:5]([S:8][C:9](=O)[CH3:10])([CH3:7])[CH3:6])[CH3:2].C[O-].[Na+].BrCC[CH2:19][C:20]([F:23])([F:22])[F:21]>CCO>[CH2:1]([O:3][C:4](=[O:12])[C:5]([CH3:7])([S:8][CH2:9][CH2:10][CH2:19][C:20]([F:23])([F:22])[F:21])[CH3:6])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 149 g (0.785 mol) of 2-acetylsulfanyl-2-methyl-propionic acid ethyl ester in EtOH (1.2 L, degassed under nitrogen for 1 h) are added 169.7 g (0.105 mol) of sodium methoxide, followed by a solution of 150 g (0.785 mol) of 4-bromo-1,1,1-trifluoro-butane. The reaction is heated to 85° C. for 3 d. The solvent is removed under reduced pressure. The residue is dissolved in DCM (1 L) and washed with saturated aq. NaHCO3 solution (2×1 L). The organic layer is dried over Na2SO4, filtered and the filtrate is concentrated under reduced pressure to afford 171 g of 2-methyl-2-(4,4,4-trifluoro-butylsulfanyl)-propionic acid ethyl ester. Yield: 84%; ESI-MS: 259 [M+H]+

Workup

customThe solvent is removed under reduced pressure
dissolutionThe residue is dissolved in DCM (1 L)
washwashed with saturated aq. NaHCO3 solution (2×1 L)
dry with materialThe organic layer is dried over Na2SO4
filtrationfiltered
concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record: ord-09be35502f674df1b33e3e0e7dcb1eef
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865744B1

Reaction notes

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